The preparation of 4-methyl-3-decen-5-one was described in US Patent Application Publication No. 2006/0178291 A1 via the Oppenauer oxidation reaction using 45 mol % of aluminum isopropoxide and 3 equivalents of acetone based on the starting material 4-methyl-3-decen-5-ol. This reaction generates a large amount of solid waste due to the use of aluminum isopropoxide during industrial manufacturing. The solid aluminum waste is an environmental hazard and requires costly disposal.
Villa et al. reported oxidation of allylic alcohols such as cinnamyl alcohol using Au—Pd catalyst supported on carbon nanotubes. See Villa, et al., Catalysis Today 157, 89 (2010). Abad et al. studied the oxidation of secondary allylic alcohols to their corresponding ketones using gold nanoparticles deposited on nanocrystalline cerium oxide. See Abad et al., Angewandte Chemie International Edition 44, 4066 (2005) and Chemical Communications 2006, 3179. Other catalysts for oxidizing allylic alcohols include manganese dioxide, Osmium tetraoxide, Pt/Bi/graphite, and chromic acid. See Gritter et al., J. Org. Chem. 24 (8), 1051-56 (1959); Cha et al., Tetrahedron 40(12), 2247-55 (1984); Lee et al., Green Chemistry 2, 279-82 (2000); Harding et al., J. Org. Chem. 40, 1664-65 (1975). None of these oxidation reactions have been applied to prepare 4-methyl-3-decen-5-one.
There is a need to develop an efficient and environment friendly process to prepare 4-methyl-3-decen-5-one at large scale.